Our Biggest Regret

Summary

Motley Fool Money – "Our Biggest Regret"

September 8, 2025

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Episode Overview

This episode of Motley Fool Money centers on investing regrets—particularly ill-timed sells—and the lessons investors can glean from them. Host Rick Menaras is joined by regular analysts Jason Hall and Lou Whiteman. The team candidly shares their most painful sell decisions, examines why regret is unavoidable in investing, and then pivots to discuss stocks poised to benefit from potential market shifts in the near future. The episode’s tone is warm and conversational, blending personal anecdotes with actionable investing wisdom.

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Key Discussion Points & Insights

1. Discussion of Biggest Investing Regrets

[00:00–06:39]

Lou Whiteman’s Regrets

• Lou admits he isn't the type to regret missing out on meteoric winners like Amazon or Tesla because he avoids high-flying early-stage stocks.
• Key regrets:
  • Exos Financial (online bank) – up ~200% since he sold
  • Lowe’s Financial/Hotel Conglomerate – almost a double since he sold
• Reason for the regret: He “sold them without any good reason,” simply because he was bored or distracted by shinier options.
  • Quote:

    “This is the danger of acting on the whim instead of with real intent.” (Lou, [01:46])

Jason Hall’s Regrets

• Tesla: Bought in 2016, sold for a small profit—now up 2,000% (Rule Breakers portfolio: 16,000%).
• Nvidia: Sold half two years ago—up 446% since, and “never been below the price I sold.”
• Microsoft: Sold in 2013 when Steve Ballmer left and Nadella replaced him.
  • Biggest regret: Selling Microsoft out of “impatience” at exactly the wrong time; since then, it’s become an 18-bagger.
  • Quote:

    “I sold entirely because I just ran out of patience at really the absolute wrong time to have been running out of patience with Microsoft.” (Jason Hall, [03:37])

Rick Menaras’s Hardest Regret

• Netflix: Bought 500 shares in 2002 (broken IPO). After splits, could have had 7,000 shares worth $8.7 million today but “sold 99% of my shares over 23 years.”
• Major sell: Offloaded 80% of Netflix shares “a couple of months into my shareholder tenure.”
  • Quote:

    “I have 100,000 bagger in my portfolio and it’s killing me.” (Rick, [03:53])

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2. How to Avoid Investing Regrets

[04:37–06:39]

• Lou: It’s not about never selling—it’s about having a clear process and sound reasons.
  • “You have to have a reason. You have to have a process and stick with it.” (Lou, [04:44])
• Sell for valid reasons: thesis change, loss of conviction, funding life events.
• Avoid knee-jerk moves: Don’t chase shiny objects, and have a plan.
• Jason advocates for “regret minimization”—learn from mistakes, but don’t let them rule you.
  • Quote:

    “Making short-term decisions with long-term investments…that’s a lot of times the things that leads us to sell too soon.” (Jason, [05:45])

• Rick’s main takeaway:
  • “You should never buy a stock just because it goes down…and…you also shouldn’t sell a stock just because it goes up.” ([06:39])

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3. Stocks to Watch for Rate-Cut Environment

[07:41–13:30]

Jason Hall on Starbucks (SBUX)

• Thesis: Opportunity well beyond rate cuts—a turnaround is underway.
  • Shares have been on a rough, volatile six-year streak with negative comps (comparable sales).
  • Cites Brian Niccol’s recent appointment as a possible catalyst.
  • “Positive momentum” and “exceptionally low expectations” set SBUX up to potentially beat in the next quarter.
  • Quote:

    “Starbucks looks like it’s finally working through years of problems that have hurt the business. […] There have been signs of life.” (Jason, [08:39]–[09:35])

Lou Whiteman on Montrose Environmental (MEG)

• Thesis: Rate cuts could help, but the business is compelling on its own.
  • This small-cap environmental services roll-up is leveraged but has room to grow if debt costs fall.
  • They offer water and air quality monitoring and hold a slate of patents in microplastics cleanup.
  • Their consolidation strategy enables them to serve large, national clients.
  • Quotes:

    “[Montrose] provide necessary services—environmental cleanup and monitoring. These are long-term needs.” (Lou, [10:55])
    “Find a consolidator in a fragmented sector, and you can make a lot of money that way.” (Rick, [12:14])

Rick Menaras on Zillow Group (ZG)

• Thesis: As rates fall, housing market activity will revive, benefiting Zillow’s portal and ad revenue.
  • 243 million average monthly users makes it a market leader.
  • “Zillow lights the housewarming candle on both ends”—more buyers, more sellers, both increase advertising demand.
  • Revenue and earnings growth have returned, though the stock is flat over five years.
  • Quote:

    “Zillow is back to posting double digit revenue growth…and adjusted earnings is growing even faster. It’s doing well now. It should really be doing well a few months from now.” (Rick, [13:21])

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4. Game – Double Trouble

[14:56–17:58] (A rapid-fire quiz on which stocks have doubled or halved in 2025, with playful banter and insight.)

• Freshpet (FRPT): Trouble; down 63% ([15:30])
• Wayfair (W): Double; up 103% ([15:59])
• Banco Santander (SAN): Double; up 110% ([16:34])
• C3AI (AI): Trouble; down 55% due to widening losses and declining revenue ([16:59])
• Newegg Commerce (NEGG): Double; up 452%, riding the meme-stock wave ([17:33])

Humor highlight – speculation on whether the trio could make a good boy band.

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Memorable Quotes & Moments

• “This is the danger of acting on the whim instead of with real intent.” —Lou Whiteman [01:46]
• “I sold entirely because I just ran out of patience at really the absolute wrong time to have been running out of patience with Microsoft.” —Jason Hall [03:37]
• “I have 100,000 bagger in my portfolio and it’s killing me.” —Rick Menaras [03:53]
• “It’s part of the process and hopefully sharing these stories with others that have made mistakes…helps you out a little bit too.” —Jason Hall [06:20]
• “Never buy a stock just because it goes down…likewise, don’t sell just because it goes up.” —Rick Menaras [06:39]
• “Find a consolidator in a fragmented sector, and you can make a lot of money that way.” —Rick Menaras [12:14]

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Timestamps of Notable Segments

• 00:00–03:53: Personal stories of biggest selling regrets
• 04:37–06:39: How to minimize regret and improve sell discipline
• 07:41–13:30: Featured stocks for a rate-cut environment: Starbucks, Montrose Environmental, Zillow
• 14:56–17:58: “Double Trouble” stock performance game

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Episode Takeaways

• The most costly mistakes for investors often stem not from sell decisions due to valid concerns, but from selling on whim, impatience, or boredom.
• Regret in investing is unavoidable, but developing and sticking to a process can dramatically reduce painful errors.
• Preparedness for market cycles, concentration risk, and rebalancing are part of being a disciplined investor.
• The episode combines relatable tales of loss with optimism about future opportunities.

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For More

• Don’t miss the playful “boy band” jokes woven throughout the episode.
• The full discussion is spiced with practical advice and humor, characteristic of Motley Fool Money’s tone.

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Disclaimer: Speakers and The Motley Fool may have positions in the discussed stocks. Always do your own research before investing.

Transcript

[A]

Foreign don't go on a path to sell. Destruction. Motley Fool Money starts now. I'm Rick Menaras, and today I'm joined by two of my favorite voices in fooldom, Jason Hall. And joining us for hidden gems, Lou Whiteman. We're going to take a look at some stocks that we believe will head higher in the coming months. We're also going to play a new game called Double Trouble. But first, investors spend a long time treating their stocks as soulmates. Sometimes they should be treated as cellmates. We spend a lot of time discussing meet cutes when it comes to stock ideas. Today, I want to talk about breakups. More to the point, what's the decision to sell that you regret the most? Mine is easy, but I want to start with you, Louis, like, trying to figure out what to do with a blank spreadsheet square. Let's talk about your worst sell decision.

[B]

So I'm a terrible person to ask this because it's so boring, Rick. Not because I'm brilliant, not because, like, I don't have terrible, you know, mistakes, but rather, I don't tend to dabble in the early stage companies that get these, like, great, you know, explosions later, higher. I assure you, if I would have owned Amazon or if I would have owned Tesla back in the day, I would have sold them and I would have regretted them now. But I do have a lot of regrets, and I do think there's kind of a lesson there because they share a theme. Two really good companies I sold years ago. One, Exos Financial, the online bank. I think it's up like 200% since then. I really regret that. The other is Lowe's, not the home improvement company, but the financial hotel conglomerate. It's, I think, almost a double since then. And the similarities, the reason I regret them, these aren't the, you know, oh, my gosh, I'd be a trillionaire now. But I'll be honest. I sold them without any good reason. I had no magic process. I had no, like, you know, guiding principle. I basically got bored with them, and I saw something shinier and flashier, and that is the worst reason to sell. Not like dramatic declines. Nothing that, like, you know, this just eats at me because this is the danger of acting on the whim instead of with real intent. So every time I look at those, I kind of. I get a little sad inside.

[A]

Yeah, a lot of real world relationships end for the same reason. Lou, Jason, what's on your plate?

[C]

I could go with one that Lou mentioned. I could go with Tesla. I Bought I believe in around 2016. I sold a couple years later for a decent little profit. Stock's up 2000% since I old rule breaker investors that follow the rule breakers portfolio have enjoyed like 16,000% in wins. Owning Tesla now, clearly a financial mistake, but not sure that I regret it because I didn't sell for concerns about the business as much as just concerns about Elon Musk's ability and an interest in staying focused on Tesla and concerns about the company's ability to deliver more than just EVs and maybe batteries. I could also go with selling half of my Nvidia stake about two years ago. Stock's up 446% and it's never been below the price that I sold. I really regret that though, because I sold it because I'm at this point in my financial life where I'm thinking about position sizing and it had become such an outsized position in my portfolio. I'm still kind of okay with that decision, even though maybe I should have let that problem become a much bigger problem. But the one that I really regret. Rick I even wrote about it on fool.com in August of 2013 and that was selling Microsoft. And it was right as Steve Ballmer was leaving and set to be replaced by Satya Nadella. I sold entirely because I just ran out of patience at really the absolute wrong time to have been running out of patience with Microsoft. And it's been an 18 bagger since. Since I wrote that article and since I sold my shares.

[A]

Ouch. Jason all right, I have a story to share too. Invest long enough and you'll get a 10 bagger. If your aim is true, you may even wind up with a hundred bagger, a thousand bagger, a ten thousand bagger, or understandably, understandably even more rare. I have 100,000 bagger in my portfolio and it's killing me. I bought 500 shares of Netflix in October 2002 when it was a broken IPO. Just a few months after hitting the market after pair of stock splits, I would have 7,000 shares worth $8.7 million today. Unfortunately, I have sold 99% of my shares over the past 23 years. I sold 80% just a couple of months into my shareholder tenure. And I regret that a lot more than the other 19% I pared back much later as the position became a larger part of my portfolio.

[B]

My heart goes out to all of us and terrible stories. I also I don't think we should be afraid to sell. And if anything, I feel like I should be more open to selling if for the right reasons. I think you can make bad decisions if you refuse to sell. But again, I come back to it kind of looking at mine. You have to have a reason. You have to have a process and stick with it. If the thesis has changed, you should probably sell. If you don't believe it anymore, it's selling because you actually want to use the money for a life event. If you're going to get married or you have kids that look, hey, that's a reason to sell. We're going to use the money. But buying or selling, I've tried to work on being more purposeful, to slow things down, to not react, not look for shiny objects. I think you can avoid the worst regrets by just have a plan, stick to it. It's just, gosh, Jason, there's so much stimulus coming at us. How do you stay on a plan?

[C]

Yeah, Lou, you're right. I think regret minimization is something that as investors we have to sharpen that skill. Right. And really build that muscle. And that doesn't mean ignoring mistakes and pretending like they don't happen. You have to learn from them. But one of the things that I've learned to do is to build a framework that helps me reduce those, the unforced errors. You know, basically making short term decisions with long term investments, that that's a lot of times the things that leads us to sell too soon. And better align my actions with all of my financial goals, whether they are the long term ones, but also the short term ones too. Right. Aligning those decisions based on what the asset itself is, I think can be one of the most important steps to take. It's certainly the one that's helped me avoid most of the worst mistakes. And you know what? My heart doesn't go out to you, Rick. My heart doesn't go out to you, Lou. I don't feel sorry for myself here because I look at my portfolio and over mistakes are part of the process. And I know all three of us have done quite well and we're set up to reach all of our short term and long term financial goals. So it's part of the process and hopefully sharing these stories with others that have made mistakes. Fools listening. I hope this kind of helps you out a little bit too.

[A]

Yeah. My lesson is that you should never buy a stock just because it goes down. And by the same, I guess, metrics, you also shouldn't sell a stock just because it goes up. And I agree with you both, not dwelling on the selling, Learn something and move on. Or in the words of Nicole Kidman and as she walks into an MT AMC theater, somehow heartbreak feels good in a place like this. Coming up next, we shift gears to talk about stocks we like right now. Lou Jason, we're not a boy band yet, but like NSync, we're going to go over some buy buy buys.

[B]

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[A]

Pressure on Friday after a weak jobs report made it even more likely that the Fed will start to cut rates later this month. Every move creates an opportunity. I want to go around the room and see what stocks on your is on your radar as a potential buy ahead of what could be three months of small but potent, potent rate cuts. Jason what's one stock you think will rise in the fall?

[C]

You know, I'm going to go on a limb here and I'm going to bring up one that I don't think that rate cuts directly are the reason that the stock is going to go up. And I'm going to give you a hot take on Starbucks. I'm going to give it to you in a lot less time than it would have taken you to get your favorite cup of caffeine from that coffee giant over the past couple of years. Starbucks shares are basically on a six year, highly volatile losing streak. Revenue growth is stalled. Tons of legit competition has emerged all over the world. We've got another IPO that's coming up pretty soon in that coffee space. I know that sounds like a terrible stock to expect to go up, right?

[A]

Rick yeah, but you have me percolating. Jason why do you think Starbucks will rise in the fall?

[C]

In short, Starbucks looks like looks like it's finally working through years of problems that have hurt the business. And those problems were happening before we realized they were problems. The collision vision of too much technology that was driving a ton of orders was it ran into too much complexity behind the counter, along with a number of other poor operational decisions, hurt the customer experience, hurt the company's relations with its workers. Here's a stat. Starbucks hasn't had a positive quarter of comps that's that important measure of retail, of sales at stores that have been open for at least one year has has a a positive comps quarter since the end of 2023. That's seven straight negative comp quarters. Seriously now, Brian Nickel, I, I believe is the best operator in the restaurant industry, was brought in just 13 months ago to fix really a broken business that's attached to an incredible brand. There have been signs of life. The past couple of quarters comps have still been down, but much less worse than prior to Nichols implementing the Starbucks back to back back to Starbucks initiative. So when we combine that positive momentum over the past six months with a really brutal comp period that was last year's fall quarter, it was particularly bad. Comps were down a brutal 7%. I think the combination of low expectations and a low bar for what could look like pretty good results that set Starbucks up to beat expectations when it reports in October. And I think there's going to be momentum that can drive the stock up.

[A]

Yeah, let's hope so. Lou, tell us about a stock that you like here.

[B]

So conventional wisdom has it that small caps do better in a rate cut environment because the cost of borrowing should come down and smaller companies tend to be more on the edge when it comes to debt. So with that in mind, one I'm watching is a stock called Montrose Environmental Ticker. Meg, they're only about a billion dollar market cap. They're a roll up and they're an active acquirer. So they have a lot of debt, specifically 330 million debt compared to just like 11 million in cash. They're the type of company that that gets a longer lifeline or life gets a lot easier for them if their cost of debt can come down.

[A]

Lou, I remember you writing about Montrose a couple years ago and it was a beneficiary of COVID related testing. Why? Do you think it will rise in the fall?

[B]

Yeah, that was kind of more of a distraction. I mean but what they do at a core they provide necessary services with chart environmental cleanup and environmental air quality monitoring, water quality monitoring. These are long term needs, Rick. These are things that we just any administration, whatever's going on, there's a need for this. Montrose has a of patents in areas like neutralizing microplastics and getting them out of the water. What sets them apart for me is this rollup. It is a risk. But they are in an industry full of basically small and regional players. They are a national player, they've been a consolidator, they have the scale to take on bigger projects and also large corporate customers that have operations all over the country. They have the option with Montrose to just do business with one vendor. Like, if you're a mining company, you can work with them nationwide instead of having to find a partner in every market they operate. This is no sure thing, but it's intriguing. And if they can get borrowing rates down, their odds of success improve.

[C]

One of the things that's so compelling about what you're talking about, Lou, is the market is littered with these sleepy little underappreciated companies in markets like that that are massively fragmented, that have a good record of rolling up and consolidating. So I think that's what.

[B]

It's just expensive. And if the debt gets cheaper, just life gets easier.

[A]

Yeah. Find a consolidator in a fragmented sector, and you can make a lot of money that way. My stock is Zillow Group. There are two classes of shares here, but I'm going with the class A voting stock. Trading under the ticker symbol ZG, Zillow operates the leading residential real estate portal with 243 million average monthly unique users.

[C]

Wow. Housing, not a beautiful market right now. Rick, what's got you thinking that Zillow can rise in the fall?

[A]

Yeah. So financing rates start moving markedly lower in the coming months. It's going to breathe new life into the depressed residential real estate market that has seen its transaction volume inch just 1 to 2% higher over the past year. Demand will spike as homebuyers cash in on getting more bang for their mortgage buck. Supply will also finally start to ease once homeowners aren't afraid to cash out of their low rates on existing digs. Zillow lights the housewarming candle on both ends. The surge in demand creates more app and website traffic, and that's a dinner bell for the real estate agents and other advertisers paying for exposure to this lucrative audience. More homes hitting the market will make it even more important to pay up to stand out on the platform. Zillow Stack is beating the market over the past year, but it's also flat with where it was five years ago. It doesn't seem fair. Zillow is back to posting double digit revenue growth and adjusted earnings is growing even faster. It's doing well now. It should really be doing well a few months from now.

[B]

Rick, I love the stock idea, but I'm more intrigued with the three of us as a boy band. We need to talk about that more after this is over.

[A]

Oh, we will. In Harmony. When we get back, I break out a new game to see if Jason and Lou can sort this year's biggest gainers from its biggest losers. Stick around. We'll end the show in sync. Hey, fools.

[D]

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[A]

Jason Lou, from our Culture Exchange program with hidden gems. Let's play double trouble and let's go over the rules because it's a brand new game. I will mention a stock that's been on the move this year. If you think it has more than doubled, say double. If you think it's lost more than half of its value in 2025, say trouble. Simple enough. Let's go first, one fresh pet FRPT the company behind refrigerated dog and cat food. Double or trouble?

[C]

Jason, I'm going to say trouble.

[B]

You know, I hear about it so much, but maybe. I was going to say double. Well, just let's have fun.

[A]

We are having fun. But Jason is right. Trouble down 63%. Freshmen is still posting double digit sales growth, but it began the year with a steep valuation that's high even in dog years here. So next up, Wayfair ticker symbol W Online furniture retailer. We probably know this company. Double or trouble? Lou?

[B]

I haven't personally bought anything in a while, but I think other people have. I'll say double here.

[C]

I think it's bounced back. It's struggled so much coming out of the pandemic. I think there's been a little bit of a recovery.

[A]

Yeah, it's been a quite A recovery at least for the stock. Up 103%. So a double. You are both correct. Wayfair is gaining market share during a cyclical downturn, but in its latest quarter, adjusted earnings nearly doubled. Third up, we're traveling far away for Banco Santander. San is a ticker symbol, Spain's largest bank. Double or trouble? Start with you, Jason.

[C]

Oh, man, I think I'm wrong here, but I'm going to say double because I know European banks have just taken it on the chin, but I think there's some life coming back into that sector.

[B]

Yeah, definitely double for me. Just where Europe's going.

[A]

Yeah. Up 110%. The banking giant has been expanding across Europe and Latin America for some time. And earlier this year it formed a partnership with Verizon to boost its presence in the U.S. u.S. Next up, C3AI ticker symbol AI, a provider of AI software tools for the energy industry and other enterprises. Double or trouble?

[B]

Lou, this is trouble.

[C]

Yeah, absolutely. Trouble. I don't want to get sued, so I'm not going to say anything but trouble.

[A]

Yeah. Down 55%. Net losses keep widening and revenue is now going the wrong way. So having some challenges there, despite it's awesome. Ticker symbol for the times. Finally, Newegg Commerce Negg, Consumer Electron. Double or trouble?

[C]

Jason, I'm going to say double. I'm making a wild guess here completely coming from the perspective of a consumer of computer electronics. They're still the gold standard.

[B]

They were crazy a while ago, they've come back to earth. But I'm guessing it's, it's got a, it's not trouble. It's got to be a double.

[A]

Yeah, not just a double. Up 452% still. Wow. Yeah. Revenue growth has turned positive in 2025 after three years of decline. So that's the good thing. But what's really carrying it is mostly the fact it's riding the new wave of meme stock. So that's happening right now for that stock. But clearly a company that's fundamentals at least are starting to turn the corner. Jason and Lou, thank you for going over the highs and lows of investing and price moves with me today. If you want to give the boy band a shot, we can try, try, try.

[B]

Rick, I'm bullish. You're a double.

[A]

That sounds like trouble. Thank you, thank you, thank you. To the two of you, a double dose of wizards wisdom. To my, to my, my me them. As always, people on the program may have interest in the stocks they talk about and the motley fool may have formal recommendations for or against, so don't buy or sell stocks based solely on what you hear. All personal finance content follows Motley fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosures, please check out our show notes for Jason Hall, Lou Whiteman and the entire Motley Fool Money team. I'm Rick Menares. May your days be sunny and your life Motley Fool Money.